Dear Meredith,

I’ve had a big crush on “Jake” for five years. We work in the same industry, and when we met there was an immediate spark. He was married at the time, so I tried to put him out of my mind. Over the next few years, we’d see each other at numerous work events around the city and we always had a great time talking and hanging out.

A year and a half ago, I found out that Jake was going through a divorce. Needless to say, this reignited my crush on him big time. I also found out that he had a girlfriend for a few months right after he was separated.

Last fall we were back in touch and started meeting up as friends and then (finally!) started dating. There were intense sparks and a clear connection. We also talked about deep, important things and connected on a more personal level. After about six week of dating, we had another great date night and I went back to his house for the first time – we hooked up but didn’t have sex, and I didn’t stay over because he had an early-morning flight. After that night, he ghosted. He stopped reaching out, he barely texted me back; something had changed. I gave him space and reached out after a month to ask what had happened. He said he really liked me and would love to continue to hang out, but couldn’t offer anything more in terms of a relationship right now (he acknowledged that we’d never actually talked about our status, but it seemed like it was headed that way before he ghosted).

He added that sometimes he just disappears in order to deal with the new reality of his life (being divorced), and that the holidays are especially tough. I said I completely understood and would be happy to hang out as friends. Over the past few weeks, we’ve starting to hang out again as friends, going out for drinks, a hike, and playing tennis, but there is still an attraction and connection and our texts are beyond flirty. I haven’t pushed for anything more and neither has he. Here’s my dilemma: I can’t discern if he not interested in dating anyone right now, or if he’s just not that into me. He’s been my crush (and sometimes more) for SO long that I need to know one way or another if there is a future here or not. I either need put this crush to bed for good, or decide if I want to wait for him to be ready to date again.

Should I ask him if he could see a future for us or could this scare him away? Should I move on and assume that if he were into me he would have made a move by now? Is it possible that he does really like me but just isn’t ready for a serious relationship yet? Should I keep playing it cool as flirty friends and hope that one day he might be ready to really date?

– Analysis paralysis